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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Tropanole</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><p>Die <b>Tropanole</b> leiten sich vom <a href="Tropan" title="Tropan">Tropan</a> ab, wobei eine <a href="Hydroxygruppe" title="Hydroxygruppe">Hydroxysubstitution</a> am C-1, C-2- bzw. am C-3-Atom vorliegt. Für das 2- und das 3-Tropanol können zwei <a href="Stereoisomere" class="mw-redirect" title="Stereoisomere">Stereoisomere</a> unterschieden werden. Bei den α-Tropanolen steht die <a href="Hydroxygruppe" title="Hydroxygruppe">Hydroxygruppe</a> <a href="Axial_(Chemie)" title="Axial (Chemie)">axial</a>, bei dem β-Tropanolen <a href="%C3%84quatorial_(Chemie)" title="Äquatorial (Chemie)">äquatorial</a> zum Ringsystem.
</p>
<table class="wikitable left" style="text-align:center; font-size:90%;">
<tbody><tr>
<td class="hintergrundfarbe6" colspan="6"><b>Tropanole</b>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Name
</td>
<td>(<i>1R</i>)-1-Tropanol
</td>
<td>2α-Tropanol
</td>
<td>2β-Tropanol
</td>
<td>3α-Tropanol
</td>
<td>3β-Tropanol
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left">Andere Namen
</td>
<td>
<ul><li>1-Hydroxytropan</li>
<li>8-Methyl-8-azabicyclo[3.2.1]octan-1-ol</li></ul>
</td>
<td>
<ul><li>2α-Hydroxytropan</li>
<li>8-Methyl-8-azabicyclo[3.2.1]octan-2<i>endo</i>-ol</li></ul>
</td>
<td>
<ul><li>2β-Hydroxytropan</li>
<li>8-Methyl-8-azabicyclo[3.2.1]octan-2<i>exo</i>-ol</li></ul>
</td>
<td>
<ul><li>3α-Hydroxytropan</li>
<li>Tropin</li>
<li>8-Methyl-8-azabicyclo[3.2.1]octan-3<i>endo</i>-ol</li></ul>
</td>
<td>
<ul><li>3β-Hydroxytropan</li>
<li>Pseudotropin</li>
<li>8-Methyl-8-azabicyclo[3.2.1]octan-3<i>exo</i>-ol</li></ul>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Strukturformel" title="Strukturformel">Strukturformel</a>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span typeof="mw:File"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">36127-54-5</span><span class="editoronly" style="display:none;"></span></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">36127-15-8</span><span class="editoronly" style="display:none;"></span></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=120-29-6">120-29-6</a><span class="editoronly" style="display:none;"></span></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=135-97-7">135-97-7</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/268139">268139</a></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/54607705">54607705</a></td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8424">8424</a></td>
<td>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td colspan="5">C<sub>8</sub>H<sub>15</sub>NO
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td colspan="5">141,21 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>47–48 °C oder 68–70 °C<sup id="cite_ref-Römpp_1-0" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>46–48 °C<sup id="cite_ref-Sarel_2-0" class="reference"><a href="#cite_note-Sarel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td>
<td>−10 °C<sup id="cite_ref-Ayer_3-0" class="reference"><a href="#cite_note-Ayer-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Davies_4-0" class="reference"><a href="#cite_note-Davies-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td>
<td>63 °C<sup id="cite_ref-Römpp_1-1" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>108–109 °C<sup id="cite_ref-Römpp_1-2" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
<tr>
<td class="hintergrundfarbe5" align="left"><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
</td>
<td>
</td>
<td>94–95 °C<sup id="cite_ref-Ayer_3-1" class="reference"><a href="#cite_note-Ayer-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Davies_4-1" class="reference"><a href="#cite_note-Davies-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</td>
<td>229 °C<sup id="cite_ref-Römpp_1-3" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td>
<td>240–241 °C<sup id="cite_ref-Römpp_1-4" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr></tbody></table>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Das (1<i>R</i>)-1-Tropanol steht mit (<i>R</i>)-(Methylamino)cycloheptanon in einem <a href="Tautomerie" title="Tautomerie">tautomeren</a> Gleichgewicht.<sup id="cite_ref-Römpp_1-5" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p><p><span typeof="mw:File"></span>
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>Tropanole und davon abgeleitete <a href="Tropanalkaloide" class="mw-redirect" title="Tropanalkaloide">Tropanalkaloide</a> kommen in mehreren <a href="Pflanzenfamilie" class="mw-redirect" title="Pflanzenfamilie">Pflanzenfamilien</a>, insbesondere in den <a href="Nachtschattengew%C3%A4chse" title="Nachtschattengewächse">Nachtschattengewächsen</a> (<i>Solanaceen</i>) vor. Zum Beispiel im <a href="Bilsenkraut" class="mw-redirect" title="Bilsenkraut">Bilsenkraut</a> (<i>Hyoscyamus niger</i>), in der <a href="Tollkirsche" class="mw-redirect" title="Tollkirsche">Tollkirsche</a> (<i>Atropa belladonna</i>) und in verschiedenen <a href="Stechapfel" class="mw-redirect" title="Stechapfel">Stechapfel</a>-Arten (<i>Datura</i> spec.). Das (1<i>R</i>)-1-Tropanol ist in der <a href="Andenbeere" class="mw-redirect" title="Andenbeere">Andenbeere</a> (<i>Physalis peruviana</i>) zu finden.<sup id="cite_ref-Römpp_1-6" class="reference"><a href="#cite_note-Römpp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Ebenso findet sich im <a href="Echtes_L%C3%B6ffelkraut" title="Echtes Löffelkraut">Echten Löffelkraut</a> (<i>Cochlearia officinalis</i>, <a href="Brassicaceae" class="mw-redirect" title="Brassicaceae">Brassicaceae</a>) das Cochlearin mit Tropin als Alkoholkomponente. Die anderen Familien sind: <a href="Proteaceae" class="mw-redirect" title="Proteaceae">Proteaceae</a>, <a href="Convolvulaceae" class="mw-redirect" title="Convolvulaceae">Convolvulaceae</a>, <a href="Euphorbiaceae" class="mw-redirect" title="Euphorbiaceae">Euphorbiaceae</a>, <a href="Rhizophoraceae" class="mw-redirect" title="Rhizophoraceae">Rhizophoraceae</a> und <a href="Erythroxylaceae" class="mw-redirect" title="Erythroxylaceae">Erythroxylaceae</a>. Es konnte nachgewiesen werden, dass die Entwicklung der zur <a href="Biosynthese" title="Biosynthese">Biosynthese</a> nötigen Enzyme in Nachtschatten- und Rotholzgewächsen unabhängig voneinander stattfand.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Römpp-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Römpp_1-0">a</a></sup> <sup><a href="#cite_ref-Römpp_1-1">b</a></sup> <sup><a href="#cite_ref-Römpp_1-2">c</a></sup> <sup><a href="#cite_ref-Römpp_1-3">d</a></sup> <sup><a href="#cite_ref-Römpp_1-4">e</a></sup> <sup><a href="#cite_ref-Römpp_1-5">f</a></sup> <sup><a href="#cite_ref-Römpp_1-6">g</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-20-03276"><i>3α-Tropanol</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 29. Januar 2013.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sarel-2"><span class="mw-cite-backlink"><a href="#cite_ref-Sarel_2-0">↑</a></span> <span class="reference-text">S. Sarel, E. Dykman: <i>Hypoiodate-induced oxidative dimerization and functionalization of the tropane bicyclic system.</i> In: <i><a href="Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a></i> 17, 1976, S. 3725–3728, <a href="https://doi.org/10.1016/S0040-4039(00)93093-4" class="extiw external" title="doi:10.1016/S0040-4039(00)93093-4">doi:10.1016/S0040-4039(00)93093-4</a>.</span>
</li>
<li id="cite_note-Ayer-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Ayer_3-0">a</a></sup> <sup><a href="#cite_ref-Ayer_3-1">b</a></sup></span> <span class="reference-text">D. E. Ayer, G. Büchi, P. R. Warnhoff, D. M. White: <i>The structure of dioscorine.</i> In: <i><a href="Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i> 80, 1958, S. 6146–6146, <a href="https://doi.org/10.1021/ja01555a061" class="extiw external" title="doi:10.1021/ja01555a061">doi:10.1021/ja01555a061</a>.</span>
</li>
<li id="cite_note-Davies-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Davies_4-0">a</a></sup> <sup><a href="#cite_ref-Davies_4-1">b</a></sup></span> <span class="reference-text">W. A. M. Davies et al.: <i>703. An alkaloid of Dioscorea hispida, Dennstedt. Part VI. Some investigations on the synthesis of tropan-2-one.</i> In: <i><a href="Journal_of_the_Chemical_Society" title="Journal of the Chemical Society">Journal of the Chemical Society</a>.</i> 1960, S. 3504–3512, <a href="https://doi.org/10.1039/JR9600003504" class="extiw external" title="doi:10.1039/JR9600003504">doi:10.1039/JR9600003504</a>.</span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">J. Jirschitzka, G. W. Schmidt et al.: <i>Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae.</i> In: <i><a href="Proceedings_of_the_National_Academy_of_Sciences_of_the_United_States_of_America" title="Proceedings of the National Academy of Sciences of the United States of America">Proceedings of the National Academy of Sciences of the United States of America</a>.</i> Band 109, Nummer 26, Juni 2012, S. 10304–10309. <a href="https://doi.org/10.1073/pnas.1200473109" class="extiw external" title="doi:10.1073/pnas.1200473109">doi:10.1073/pnas.1200473109</a>. <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/22665766?dopt=Abstract">PMID 22665766</a>. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3387132/">PMC 3387132</a> (freier Volltext).</span>
</li>
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